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2-Methoxyethylamine → N-(2-Hydroxy-4-nitrophenyl)-N'-(2-methoxyethyl)urea

HRID 368381
ノート
印刷プレビュー

反応式

HRID 368381 の反応式
[Si]([O:8][C:9]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=1[NH2:11])(C(C)(C)C)(C)C.Cl[C:20](Cl)([O:22]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[CH3:38][O:39][CH2:40][CH2:41][NH2:42]>C1(C)C=CC=CC=1>[OH:8][C:9]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=1[NH:11][C:20]([NH:42][CH2:41][CH2:40][O:39][CH3:38])=[O:22]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 154857102-[(Tert-butyldimethylsilyl)oxy]-4-nitroaniline

生成物 1

HCID 23288457N-(2-Hydroxy-4-nitrophenyl)-N'-(2-methoxyethyl)urea収率 124.1%

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-tert-butyldimethylsilyloxy-4-nitroaniline (200 mg, 0.75 mmol) in toluene (5 mL), triphosgene (84 mg, 0.3 mmol) and triethylamine (0.13 mL, 0.9 mmol) were added. The reaction mixture was stirred at 80° C. for 3 hours. Then it was cooled to room temperature and all solvent was evaporated. The residue was dissolved in DMF (1 mL) and 2-methoxyethylamine (56.3 mg, 0.75 mmol) was added. The reaction mixture was stirred at 80° C. for 16 hours. Chromatography of the resulting liquid on silica gel (50% Ethyl acetate/Hexane) gave desired product (95 mg, 50%). EI-MS m/z 256.2 (M+). mp: 190.0-190.7° C.

後処理

  1. temperatureThen it was cooled to room temperature
  2. customall solvent was evaporated
  3. dissolutionThe residue was dissolved in DMF (1 mL)
  4. stirringThe reaction mixture was stirred at 80° C. for 16 hours

出典と根拠

ORDレコード
ord-e32a29067b2640b49c7c561dd85cfe3c
出典データセット
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06133319

反応ノート

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